Sodium Cyanide → tert-Butyl-4-(cyanomethyl)-3-chlorobenzoate

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Reaction Conditions

Reaction Steps

The foregoing compound was dissolved in DMF (3 mL) and cooled to 0° C. NaCN (2 equ) dissolved in 1 mL of water and 2 mL of DMF were added to the solution and the reaction mixture was stirred for 0.5 h. After diluting the mixture with ethyl acetate it was washed with aqueous ammonium sulfate and brine, dried (Na2SO4), filtered and evaporated to give a yellow solid which was directly used in the esterification step. 2-(2-Chloro-4-carboxyphenyl)-acetonitrile (0.391 g, 2 mmol) was treated with 2 equiv of isourea 4 in 35 mL of DCM at reflux over night. After evaporation of DCM, the crude was diluted in EtOAc (50 mL) and filtered. The filtrate was concentrated and purified by flash chromatography in silica gel eluting with 1% EtOAc in petroleum ether to give tert-Butyl-4-(cyanomethyl)-3-chlorobenzoate (0.24 g, 47% yield). 1H NMR (CDCl3, 400 MHz) δ 8.03 (d, J=1.6 Hz, 1 H), 7.93 (dd, J=8.02 Hz, J=1.62 Hz, 1 H), 7.60 (d, J=8.02 Hz, 1 H), 3.89 (s, 2 H), 1.61 (s, 9 H).

Provenance & Evidence